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Matsuda-Heck Arylation of Glycals for the Stereoselective Synthesis of Aryl C-Glycosides
- The methoxymethyl-protected glycal L-amicetal, synthesized de novo from L-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly trans-diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl C-glycosides in moderate to excellent yields. The products can be further functionalized, e.g., by hydrogenation, epoxidation, or dihydroxylation to furnish 2,3,6-tridesoxy, 2,3-anhydro-6-desoxy, or 6-desoxy aryl C-glycosides, respectively. The method was applied to the synthesis of an a-configured 6-desoxy-gliflozin derivative.
| Author details: | Fabian OtteORCiDGND, Bernd SchmidtORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1021/acs.joc.9b02410 |
| ISSN: | 0022-3263 |
| ISSN: | 1520-6904 |
| Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/31615205 |
| Title of parent work (English): | The journal of organic chemistry |
| Publisher: | American Chemical Society |
| Place of publishing: | Washington |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2019 |
| Publication year: | 2019 |
| Release date: | 2020/10/06 |
| Volume: | 84 |
| Issue: | 22 |
| Number of pages: | 14 |
| First page: | 14816 |
| Last Page: | 14829 |
| Funding institution: | Deutsche Forschungsgemeinschaft (DFG)German Research Foundation (DFG) [Schm1095/6-2] |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| DDC classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Peer review: | Referiert |
